EP1535940A1 - Procédé pour la préparation de polymères ayant comme groups terminaux organyloxysilyle. - Google Patents

Procédé pour la préparation de polymères ayant comme groups terminaux organyloxysilyle. Download PDF

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Publication number
EP1535940A1
EP1535940A1 EP04027418A EP04027418A EP1535940A1 EP 1535940 A1 EP1535940 A1 EP 1535940A1 EP 04027418 A EP04027418 A EP 04027418A EP 04027418 A EP04027418 A EP 04027418A EP 1535940 A1 EP1535940 A1 EP 1535940A1
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formula
polymers
radicals
optionally substituted
optionally
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German (de)
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EP1535940B1 (fr
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Wolfgang Dr. Ziche
Wolfram Dr. Schindler
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Wacker Chemie AG
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Wacker Chemie AG
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/71—Monoisocyanates or monoisothiocyanates
    • C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S528/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S528/901—Room temperature curable silicon-containing polymer

Definitions

  • the invention relates to a process for the preparation of organyloxysilyltermin faced Polymers that are resistant to humidity have increased stability, and containing such polymers crosslinkable masses.
  • Moisture-crosslinkable preparations are generally known especially those based on silyl-functionalized polymers. Among these, in turn, are those with terminal ones Alkoxysilyl groups are preferred because the cleavage products are not corrosive and toxicologically harmless.
  • the silyl-functionalized Polymers are prepared by known methods. It is known e.g. the implementation of polymers, the end groups with active hydrogen, with isocyanates, especially Isocyanatoalkyl alkoxysilanes. The reaction can be with or without carried out the isocyanate-promoting catalysts become. In EP 931 800 A, the preparation becomes silane-functional Polyurethanes of hydroxy functional prepolymers and e.g.
  • EP 372 561 A describes the preparation of a silane-crosslinkable Polyethers described that stored under exclusion of moisture must be, since he with or without silane condensation catalyst vulcanized. That this precaution is independent from the production process of the silane-crosslinkable polyether EP 397 036 A can be taken: here is a polyether only with e.g. Allylend phenomenon provided and then preferred reacted with alkoxyhydridosilanes. Again, it is described that premature even without a silane condensation catalyst Vulcanization takes place.
  • silane condensation catalysts Compounds, such as e.g. Dialkyltin (IV) compounds, such as dibutyltin dilaurate, various metal complex compounds (chelates and Carboxylates), e.g. of titanium, bismuth, zirconium, and amines their salts and other known acidic and basic catalysts.
  • Dialkyltin (IV) compounds such as dibutyltin dilaurate, various metal complex compounds (chelates and Carboxylates), e.g. of titanium, bismuth, zirconium, and amines their salts and other known acidic and basic catalysts.
  • catalysts which the isocyanate reaction with hydroxyl groups are often those that also promote silane condensation, e.g. Dialkyltin (IV) compounds and metal complex compounds (chelates and carboxylates) of bismuth and zinc or tertiary amine compounds.
  • the invention relates to a process for the preparation of organyloxysilyl-terminated polymers of the formula R 2 3-n (OR 1 ) n Si-R-NH-C (O) -OAOC (O) -NH-R-Si (OR 1 ) n R 2 3-n by reaction of ⁇ , ⁇ -dihydroxy-terminated organic polymers of the formula OH-A-OH with isocyanato-functional silanes of the formula R 2 3-n (OR 1 ) n Si-R-NCO in the presence of at least one catalyst selected from the group consisting of bismuth and zinc compounds, where R is divalent, optionally substituted hydrocarbon radicals having from 1 to 12 carbon atoms which may be interrupted by heteroatoms, R 1 may be identical or different and monovalent, optionally substituted hydrocarbon radicals having 1 to 12 carbon atoms, which may be interrupted by heteroatoms, means R 2 may be identical or different and monovalent, optionally substituted hydrocarbon radicals having 1 to 12 carbon atoms, which may
  • divalent radicals R are alkylene radicals, such as Methylene, ethylene, n-propylene, iso-propylene, n-butylene, iso-butylene, tert-butylene, n-pentylene, iso-pentylene, neo-pentylene, tert-pentylene radical, hexylene radicals, such as the n-hexylene radical, Heptylene radicals, such as the n-heptylene radical, octylene radicals, such as the n-octylene radical and iso-octylene radicals, such as the 2,2,4-trimethylpentylene radical, Nonylene radicals, such as the n-nonylene radical, decylene radicals, such as the n-decylene radical, dodecylene radicals, such as the n-dodecylene radical; Alkenylene radicals, such as the vinylene and
  • Radical R is preferably divalent hydrocarbon radicals with 1 to 6 carbon atoms, more preferred divalent hydrocarbon radicals having 1 to 3 carbon atoms, especially the methylene radical.
  • radical R 1 and R 2 are each independently of one another alkyl radicals, such as the methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, tert-butyl, n-butyl Pentyl, iso-pentyl, neo-pentyl, tert-pentyl, hexyl, such as n-hexyl, heptyl, such as the n-heptyl, octyl, such as the n-octyl and iso-octyl, such as 2, 2,4-trimethylpentyl radical, nonyl radicals, such as the n-nonyl radical, decyl radicals, such as the n-decyl radical, dodecyl radicals, such as the n-dodecyl radical; Alkenyl radicals, such as the vinyl and allyl radicals
  • substituted radicals R 1 are alkoxyalkyl radicals, such as, for example, ethoxy and methoxyethyl radicals.
  • Radicals R 1 and R 2 are each, independently of one another, a hydrocarbon radical having 1 to 6 carbon atoms, more preferably an alkyl radical having 1 to 4 carbon atoms, in particular the methyl radical.
  • radical A examples include divalent polymer radicals, such as polyether radicals of the general formula - (R 3 O) m -, wherein R 3 may be identical or different and optionally substituted hydrocarbon radicals, preferably methylene, ethylene and 1,2-propylene radicals, and m is an integer from 7 to 600, preferably 70 to 400, (such as those commercially available under the name "Acclaim 12200" from Bayer AG, Germany, "Alcupol 12041LM” from Repsol, Spain and “Poly L 220-10 “from Arch Chemicals, USA), polyester residues, polycarbonate residues, polyester carbonate residues (eg those commercially available under the designation" Desmophen 1700 “and” Desmophen C-200 "from Bayer AG, Germany), polybutenylene residues and polybutadienylene residues (eg those commercially available under the name "Poly bd® R-45 HTLO” from Sartomer Co., Inc., USA or "Kraton TM Liquid L-22
  • n has the value 2 or 3.
  • the inventively used organic polymers of the formula (II) to form polymer preparations are those based on polyethers, of which in turn especially 1,2-polypropylene glycols having molecular weights are preferred greater than 4000, more preferably 4000 to 20000 (nominal Molecular weight).
  • the organic used in the invention Polymers of the formula (II) at 23 ° C has a viscosity of 10 to 1 000 000 mPas, more preferably from 1000 to 300 000 mPas.
  • the polymers of the formula (II) used according to the invention are commercially available products or can according to in polymer chemistry common methods are produced.
  • silanes of the formula (III) are isocyanato-methyl-dimethylmethoxysilane, Isocyanato-propyl-dimethylmethoxysilane, Isocyanato-methyl-methyldimethoxysilane, isocyanato-propyl-methyldimethoxysilane, Isocyanato-methyl-trimethoxysilane and isocyanato-propyl-trimethoxysilane, wherein isocyanato-methyl-methyldimethoxysilane, Isocyanato-propyl-methyldimethoxysilane, isocyanato-methyl-trimethoxysilane and isocyanato-propyltrimethoxysilane preferably and isocyanato-methyl-methyldimethoxysilane and Isocyanato-propyl-methyldimethoxysilane particularly preferred are.
  • silanes of the formula (III) used according to the invention are commercially available products or can according to in silicon chemistry common methods are produced.
  • Examples of the catalysts used according to the invention are zinc acetylacetonate, bismuth (2-ethylhexanoate), bismuth neodecanoate, Zinc 2-ethylhexanoate, zinc neodecanoate and bismuth tetramethylheptanedionate.
  • Examples of commercially available Catalysts are Borchi® Kat 22, Borchi® Kat VP 0243, Borchi® Kat VP 0244 (Borchers GmbH), the BICAT® grades (The Shepherd Chemical Company, USA) and K-Kat® K-348 (KING INDUSTRIES, INC., USA).
  • the invention used Catalyst for carboxylates of bismuth and zinc, whereby bismuth (2-ethylhexanoate), Bismuth neodecanoate, zinc 2-ethylhexanoate and zinc neodecanoate, or mixtures thereof are particularly preferred are.
  • catalysts are used in amounts of preferably 0.001 to 1.0 parts by weight, more preferably 0.01 to 0.5 parts by weight, based in each case on 100 parts by weight of the isocyanatosilane of the formula (III) used.
  • the process according to the invention is preferred at temperatures of 0 to 150 ° C, more preferably at 30 to 100 ° C and a Pressure of the surrounding atmosphere, about 900 to 1100 hPa, performed.
  • the inventive method can be both continuously as also be carried out batchwise.
  • the method according to the invention has the advantage of being fast and easy to carry, being readily available Raw materials are used as starting materials.
  • Another advantage of the method according to the invention is that the polymers produced can be reused directly, e.g. in the production of crosslinkable compounds.
  • the inventively prepared organyloxysilyltermin striving Polymers can be used everywhere where so far Organyloxysilylterminêt elegant polymers were used.
  • Another object of the present invention is a process for the preparation of crosslinkable compositions, characterized in that in a first step ⁇ , ⁇ -dihydroxy-terminated organic polymers of the formula OH-A-OH with isocyanato-functional silanes of the formula R 2 3-n (OR 1 ) n Si-R-NCO in the presence of catalysts selected from the group consisting of bismuth and zinc compounds, be converted to organyloxysilyl-terminated polymers, wherein R, R 1 , R 2 , A and n have the meaning given above, and in a second step the polymers (A) obtained in the first step are mixed with silane condensation catalyst (B) and optionally further substances (C).
  • silane condensation catalysts (B) containing a Vulkanisation of organyloxysilyl-terminated polymers under Influence of humidity are dibutyltin dilaurate, Dibutyltin diacetate, tetrabutyldimethoxydistannoxane, solutions of dibutyltin oxide in methyltrimethoxysilane or tetraethoxysilane, Dioctyltin dilaurate, dioctyltin diacetate, tetraoctyldimethoxydistannoxane, Solutions of dioctyltin oxide in methyltrimethoxysilane or tetraethoxysilane, dibutyltin bis (2,4-pentanedionate), Dibutyltin maleate, aminopropyltrimethoxysilane and aminoethylaminopropyltrimethoxysilane and acid catalysts, such as organic carboxylic
  • the silane catalysts (B) are Dialkyltin diacylates, amines and phosphoric acid esters, especially preferred are mono- and dialkylphosphoric acid esters and aminoalkylsilanes.
  • silane catalyst (B) in quantities of preferably 0.01 to 3.0 parts by weight, more preferably 0.1 to 1.0 parts by weight, based in each case on 100 parts by weight Polymer (A) used.
  • further substances (C) can all Components are used, which so far in networkable Masses have been used, which are preferably fillers, Additives, e.g. Adhesion promoters, UV stabilizers, Antioxidants, pigments and drying agents, crosslinkers, such as alkoxysilanes, plasticizers, e.g. Phthalates, polyethers and polybutenes, more preferably adhesion promoters, fillers and plasticizers can act.
  • Additives e.g. Adhesion promoters, UV stabilizers, Antioxidants, pigments and drying agents
  • crosslinkers such as alkoxysilanes
  • plasticizers e.g. Phthalates, polyethers and polybutenes
  • adhesion promoters e.g. Phthalates, polyethers and polybutenes
  • fillers and plasticizers can act.
  • optionally used fillers are non-reinforcing fillers, ie fillers with a BET surface area of up to 50 m 2 / g, such as quartz, diatomaceous earth, calcium silicate, zirconium silicate, zeolites, metal oxide powder such as aluminum, titanium, iron or zinc oxides or their mixed oxides, barium sulfate, calcium carbonate, gypsum, silicon nitride, silicon carbide, boron nitride, glass and plastic powders, such as polyacrylonitrile powder; reinforcing fillers, ie fillers having a BET surface area of more than 50 m 2 / g, such as fumed silica, precipitated silica, carbon black, such as furnace and acetylene black, and silicon-aluminum mixed oxides with a large BET surface area; fibrous fillers such as asbestos as well as plastic fibers.
  • non-reinforcing fillers ie fillers with a BET surface area
  • the fillers mentioned may be hydrophobic, for example by treatment with organosilanes or siloxanes or with stearic acid or by etherification of hydroxyl groups to alkoxy groups.
  • organosilanes or siloxanes or with stearic acid or by etherification of hydroxyl groups to alkoxy groups.
  • filler are amounts of preferably 1.0 to 50.0 parts by weight, more preferably 5 to 30 parts by weight, respectively based on 100 parts by weight of polymer (A).
  • additives which may be used are adhesion promoters, such as aminopropyltrimethoxysilane and aminoethylaminopropyltriethoxysilane, UV stabilizers and antioxidants, such as. those commercially available under the name Tinuvin® 292, Tinuvin® 327 and Tinuvin® 770 at Ciba Specialty Chemicals Lampertsheim GmbH, pigments, such as iron oxide, and Drying agents, such as trimethyl carbonate, vinyltrimethoxysilane and N-trimethoxysilyl-O-methyl-carbamate.
  • adhesion promoters such as aminopropyltrimethoxysilane and aminoethylaminopropyltriethoxysilane
  • UV stabilizers and antioxidants such as. those commercially available under the name Tinuvin® 292, Tinuvin® 327 and Tinuvin® 770 at Ciba Specialty Chemicals Lampertsheim GmbH
  • pigments such as iron oxide
  • Drying agents such as tri
  • crosslinkable mass additives are amounts of preferably 1 to 200 parts by weight, particularly preferably 10 to 100 parts by weight, in each case to 100 parts by weight of polymer (A).
  • crosslinkers which may be used are compounds with at least three hydrolyzable groups, such as acetoxy, Oximato and organyloxy groups, such as ethoxy, alkoxyethoxy and methoxy, which are preferably compounds with organyloxy groups.
  • crosslinker are preferably alkoxysilanes, such as vinyltrimethoxysilane, methyltrimethoxysilane, propyltrimethoxysilane, N-trimethoxysilyl-O-methyl-carbamate and N-dimethoxy (methyl) silyl-O-methyl-carbamate and / or their partial hydrolysates, wherein vinyltrimethoxysilane and N-trimethoxysilyl-O-methyl-carbamate are particularly preferred.
  • alkoxysilanes such as vinyltrimethoxysilane, methyltrimethoxysilane, propyltrimethoxysilane, N-trimethoxysilyl-O-methyl-carbamate and N-dimethoxy (methyl) silyl-O-methyl-carbamate and / or their partial hydrolysates, wherein vinyltrimethoxysilane and N-trimethoxysilyl-O-methyl-carbamate are particularly preferred.
  • crosslinkers are amounts of preferably 0.1 to 10 parts by weight, more preferably 1 to 5 parts by weight, respectively based on 100 parts by weight of polymer (A).
  • plasticizers examples include Phthalates, polyethers and polybutenes, phthalates and polyethers are preferred.
  • plasticizers are amounts of preferably 1 to 200 parts by weight, more preferably 10 to 100 parts by weight, in each case based on 100 parts by weight of polymer (A).
  • used components may each be a kind of a such component as well as a mixture of at least two Types of a respective component act.
  • the individual components be mixed together in any order; This is done with equipment that the expert for this purpose are known, such as Dissolver, planetary dissolver, planetary mixer and twin-screw kneader.
  • the second step of the method according to the invention must be extensive exclusion of humidity, as soon as silane catalyst (B) is present.
  • the second step of the method according to the invention is at Temperatures of preferably 10 to 100 ° C, more preferably at 20 to 70 ° C, and a pressure of the surrounding atmosphere, so about 900 to 1100 hPa, performed.
  • the second step of the method according to the invention can both be carried out continuously as well as discontinuously.
  • the individual steps of the method according to the invention can separately or as a so-called one-pot reaction in a reaction vessel be performed.
  • the inventive method has the advantage that the production the moisture-crosslinkable polymer in the first Step does not require exclusion of humidity.
  • The also applies to the further handling of the polymer up to the Time at which a silane condensation catalyst in the second added step according to the invention. For the user is therefore a simplified storage of even opened containers easily possible.
  • a particular advantage of the method according to the invention is that it acts as a one-pot reaction (or successive reaction in the case the continuous production) can be led, since no Deactivation of any additives or treatment of the produced silyl-functional polymer according to a the sub-steps is necessary.
  • crosslinkable compositions prepared according to the invention can used for all purposes, for which also so far Condensation / hydrolysis reaction crosslinkable at room temperature Masses have been used. They are thus excellent For example, as sealing compounds for joints, including vertical joints, and similar voids, e.g. of buildings, land, water and air vehicles, or as adhesives or greases, e.g. in the window or in the manufacture of showcases, as well as for the production of protective coatings or rubber-elastic shaped bodies as well for the isolation of electrical or electronic devices. Particularly suitable are the inventive RTV compounds as low-modulus sealing compounds for joints with possible high movement recording.
  • the usual water content of the air is sufficient.
  • the networking can at room temperature or, if desired, even at higher or lower temperatures, e.g. at -5 to 10 ° C or at 30 to 50 ° C, are performed.
  • the crosslinking is preferred performed at a pressure of the surrounding atmosphere, so about 900 to 1100 hPa.
  • the tightly closed vial is heated at 50 ° C in a water bath. Every 30 minutes, an IR measurement is performed. After 2.0 hours, the NCO band is no longer visible. There are obtained 6.74 g of a polypropylene glycol with Dimethylmethoxysilylmethyl end groups and a viscosity of 90 mPa ⁇ s.
  • the 13 C NMR spectra show the absence of undesired by-products, such as isocyanurates.
  • Example 2 The procedure described in Example 2 is repeated with the modification that used instead of 0.1 g of those used in Example 2 Catalyst mixture used 0.1 g of dibutyltin dilaurate becomes. There are 1038 g of a polypropylene glycol with trimethoxysilylmethyl end groups receive. A sample was taken in filled round aluminum cups (5 cm diameter, filling height approx. 0.5 cm) and at 23 ° C and 50% rel. Humidity stored and then the viscosity is determined. Find the results themselves in Table 1. It can be clearly seen that the viscosity undesirably increases and the polymer finally gels and becomes unusable.
  • Example 3 The procedure described in Example 3 is repeated with the modification that used instead of 0.1 g of those used in Example 3 Catalyst mixture used 0.1 g of dibutyltin dilaurate becomes.
  • a sample was filled into round aluminum dishes (5 cm diameter, filling height approx. 0.5 cm) and at 23 ° C and 50% rel. Humidity stored and then the viscosity is determined. Find the results themselves in Table 1. It can be clearly seen that the viscosity undesirably increases and the polymer finally gels and becomes unusable.
  • Example 4 The procedure described in Example 4 is repeated with the modification that 0.1 g of dibutyltin dilaurate is used instead of 0.1 g of zinc acetylacetonate. 1040 g of a trimethoxysilylpropyl-terminated polypropylene glycol are obtained. A sample was filled into round aluminum dishes (5 cm diameter, filling height about 0.5 cm) and at 23 ° C and 50% rel. Humidity stored and then determines the viscosity. The results are shown in Table 1. It can clearly be seen that the viscosity undesirably increases and the polymer finally gels and thus becomes unusable.
  • Viscosity after preparation and storage of the polymers in air (23 ° C / 50% rh)
  • aminoproyltrimethoxysilane commercially available under the trademark GENIOSIL® GF 96 from Wacker-Chemie GmbH, Germany
  • GENIOSIL® GF 96 from Wacker-Chemie GmbH, Germany
  • the mass thus obtained is now coated with a squeegee on polyethylene film applied in a thickness of 2 mm and at 23 ° C and 50% rel. Allow humidity to cross.
  • the skin formation time is 2 minutes.
  • Example 5 The procedure described in Example 5 is repeated with the modification that instead of the polymer produced in Example 2, the same amount of polymer produced in Example 3 is used.
  • the skin formation time is 15 minutes.
  • aminoproyltrimethoxysilane commercially available under the trademark GENIOSIL® GF 96 from Wacker-Chemie GmbH, Germany
  • GENIOSIL® GF 96 from Wacker-Chemie GmbH, Germany
  • the mass thus obtained is now coated with a squeegee on polyethylene film applied in a thickness of 2 mm and at 23 ° C and 50% rel. Allow humidity to cross.
  • the skin formation time is 20 minutes.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyethers (AREA)
  • Silicon Polymers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Adhesives Or Adhesive Processes (AREA)
EP04027418A 2003-11-27 2004-11-18 Procédé pour la préparation de polymères ayant comme groups terminaux organyloxysilyle. Active EP1535940B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10355318 2003-11-27
DE10355318A DE10355318A1 (de) 2003-11-27 2003-11-27 Verfahren zur Herstellung von organyloxysilylterminierten Polymeren

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EP1535940A1 true EP1535940A1 (fr) 2005-06-01
EP1535940B1 EP1535940B1 (fr) 2007-06-13

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US (1) US7319128B2 (fr)
EP (1) EP1535940B1 (fr)
JP (1) JP4908751B2 (fr)
CN (1) CN1281656C (fr)
DE (2) DE10355318A1 (fr)

Cited By (40)

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WO2006136261A1 (fr) * 2005-06-23 2006-12-28 Wacker Chemie Ag Transformation continue de polymeres analogues de monomeres de silane reactifs avec des polymeres fonctionnalises
WO2007037915A2 (fr) 2005-09-15 2007-04-05 Momentive Performance Materials Inc. Preparation de polymeres termines par amino-silane au moyen d'un catalyseur de bismuth organique et un polymere durci obtenu a partir d'un catalyseur non etain
WO2007037824A3 (fr) * 2005-09-14 2007-05-31 Momentive Performance Mat Inc Procede de production en continu de resine silylee
WO2007131912A1 (fr) * 2006-05-11 2007-11-22 Wacker Chemie Ag Mélanges polymères transparents contenant des polymères à terminaison alcoxysilane
EP1932868A1 (fr) * 2005-10-05 2008-06-18 Asahi Glass Company, Limited Polymère contenant un groupe silyle et son procédé de production
EP2064293A2 (fr) * 2006-09-18 2009-06-03 Nano-X GmbH Matériau de revêtement de silane et procédé pour la fabrication d'un revêtement de silane
DE102008021221A1 (de) 2008-04-28 2009-10-29 Henkel Ag & Co. Kgaa Härtbare Zusammensetzung auf Basis silylierter Polyurethane
WO2009133061A1 (fr) * 2008-04-28 2009-11-05 Henkel Ag & Co. Kgaa Compositions durcissables à base de polyuréthanes silylés
DE102008021222A1 (de) 2008-04-28 2009-12-24 Henkel Ag & Co. Kgaa Härtbare Zusammensetzungen auf Basis silylierter Polyurethane
DE102008038399A1 (de) 2008-08-19 2010-02-25 Henkel Ag & Co. Kgaa Härtbare Zusammensetzungen auf Basis silylierter Polyurethane
DE102008043825A1 (de) 2008-11-18 2010-05-20 Wacker Chemie Ag Verfahren zum Abdichten von Oberflächen
WO2010102916A1 (fr) * 2009-03-11 2010-09-16 Wacker Chemie Ag Procédé pour produire en continu des prépolymères à terminaison silane
DE102010028143A1 (de) 2010-04-23 2011-10-27 Wacker Chemie Ag Beschichtungszusammensetzung zum Abdichten von Oberflächen
WO2012072504A1 (fr) * 2010-11-30 2012-06-07 Henkel Ag & Co. Kgaa Produit durcissable à deux composants
DE102011003425A1 (de) 2011-02-01 2012-08-02 Henkel Ag & Co. Kgaa Härtbare Zusammensetzung mit kombinierten Stabilisatoren
DE102011081264A1 (de) 2011-08-19 2013-02-21 Wacker Chemie Ag Vernetzbare Massen auf Basis von organyloxysilanterminierten Polymeren
DE102011054615A1 (de) 2011-10-19 2013-04-25 Nano-X Gmbh Verfahren zum Herstellen von härtbaren Werkstoffen
EP2657211A2 (fr) 2012-04-26 2013-10-30 Bona GmbH Deutschland Utilisation de prépolymères fonctionnalisés par des groupes silanes dans une formulation pour la réparation de chapes
US9328259B1 (en) 2015-02-09 2016-05-03 Wacker Chemical Corporation Elastomeric silicone emulsion for coating applications
DE102016200704A1 (de) 2016-01-20 2017-07-20 Bona Gmbh Deutschland Verfahren zur Erhöhung der Anwendungssicherheit und der Alterungsbeständigkeit von Klebstoffen und anderen Produkten, enthaltend silanfunktionalisierte Präpolymere
WO2017216045A1 (fr) 2016-06-13 2017-12-21 Henkel Ag & Co. Kgaa Composition durcissable à module élevé
US9856173B2 (en) 2015-02-09 2018-01-02 Wacker Chemical Corporation One component ready-to-use tile grout
EP3336146A1 (fr) 2016-12-19 2018-06-20 Henkel AG & Co. KGaA Composition durcissable à propriétés mécaniques améliorées et transparence élevée
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CN1637043A (zh) 2005-07-13
DE10355318A1 (de) 2005-06-23
US7319128B2 (en) 2008-01-15
JP4908751B2 (ja) 2012-04-04
US20050119436A1 (en) 2005-06-02
JP2005154779A (ja) 2005-06-16
EP1535940B1 (fr) 2007-06-13
CN1281656C (zh) 2006-10-25
DE502004004076D1 (de) 2007-07-26

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